Fungicidal pyrimidine derivatives

Abstract

Fungicidal pyrimidine derivatives and the use as a fungicide of the compounds of formula (1):wherein R<1 >is H, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl C3-C6cycloalkyl, C1-C6alkoxy, C3-C6cycloalkoxy, C1-C6alylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, phenyl, pyridinyl or azolyl groups, (being optionally substituted by one or more substituents); or N(R<4>)C(O)R<5>, R<2 >is polyfluoroalkyl, R<3 >is fluorine, chlorine, bromine or iodine; ethenyl or ethynyl (being optionally substituted by one or more of halogen), R<4 >and R<5 >are, independently, H, C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl groups, (being optionally substituted by one or more of halogen or cyano); or R<4 >and R<5 >can join together to form a 5 or 6-membered ring, Q is a heteroaromatic ring selected from the following ring system; imidazol-1-yl, pyrazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-1-yl, benzimidazol-1-yl or tetrazol-5-yl groups, (being optionally substituted by one or more of substituents).

What is claimed is:  
     
       1. A pyrimidine compound represented by the formula (1),                    
       wherein R 1  is H, C 1 -C 6 alkyl (being optionally substituted by one or more of halogen), C 2 -C 6 alkenyl (being optionally substituted by one or more of halogen), C 2 -C 6 alkynyl (being optionally substituted by one or more of halogen or trialkylsilyl), C 1 -C 6 alkoxy (being optionally substituted by one or more of halogen), C 2 -C 6 alkenyloxy (being optionally substituted by one or more of halogen), C 1 -C 6 alkynyloxy (being optionally substituted by one or more of halogen), C 1 -C 6 alkylthio (being optionally substituted by one or more of halogen), C 1 -C 6 alkylsulfinyl (being optionally substituted by one or more of halogen), C 1 -C 6 alkylsulfonyl (being optionally substituted by one or more of halogen), phenyl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or alkoxy), pyridin-2-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), pyridin-3-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), pyridin-4-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), imidazol-1-yl (being optionally substituted by one or more of halogen, alkyl or alkoxy), pyrazol-1-yl (being optionally substituted by one or more of halogen, alkyl or alkoxy) or N(R 4 )C(O)R 5 ,  
       R 2  is polyfluoroC 1 -C 6 alkyl,  
       R 3  is fluorine, chlorine, bromine or iodine; ethenyl or ethynyl (being optionally substituted by one or more of halogen),  
       R 4  and R 5  are, independently, H, C 1 -C 6 alkyl (being optionally substituted by one or more of halogen); or R 4  and R 5  can join together to form a 5 or 6 membered ring,  
       Q is a heteroaromatic ring selected from the following ring system; imidazol-1-yl, pyrazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-4-yl, benzimidazol-1-yl or tetrazol-5-yl groups (being optionally substituted by one or more of halogen, cyano, hydroxy, mercapto, alkyl, haloalkyl, alkoxy, alkoxycarbonyl, amino, alkylamino, haloalkoxy, alkylthio or aralkylthio).  
     
     
       2. A fungicide for agricultural and horticultural use, comprising one or more of pyrimidine compounds represented by the formula (1)                    
       wherein R 1  is H, C 1 -C 6 alkyl (being optionally substituted by one or more of halogen), C 2 -C 6 alkenyl (being optionally substituted by one or more of halogen), C 2 -C 6 alkynyl (being optionally substituted by one or more of halogen or trialkylsilyl), C 1 -C 6 alkoxy (being optionally substituted by one or more of halogen), C 2 -C 6 alkenyloxy (being optionally substituted by one or more of halogen), C 1 -C 6 alkynyloxy (being optionally substituted by one or more of halogen), C 1 -C 6 alkylthio (being optionally substituted by one or more of halogen), C 1 -C 6 alkylsulfinyl (being optionally substituted by one or more of halogen), C 1 -C 6 alkylsulfonyl (being optionally substituted by one or more of halogen), phenyl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or alkoxy), pyridin-2-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), pyridin-3-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), pyridin-4-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), imidazol-1-yl (being optionally substituted by one or more of halogen, alkyl or alkoxy), pyrazol-1-yl (being optionally substituted by one or more of halogen, alkyl or alkoxy) or N(R 4 )C(O)R 5 ,  
       R 2  is polyfluoroC 1 -C 6 alkyl,  
       R 3  is fluorine, chlorine, bromine or iodine; ethenyl or ethynyl (being optionally substituted by one or more of halogen),  
       R 4  and R 5  are, independently, H, C 1 -C 6 alkyl (being optionally substituted by one or more of halogen); or R 4  and R 5  can join together to form a 5 or 6 membered ring,  
       Q is a heteroaromatic ring selected from the following ring system; imidazol-1-yl, pyrazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-4-yl, benzimidazol-1-yl or tetrazol-5-yl groups (being optionally substituted by one or more of halogen, cyano, hydroxy, mercapto, alkyl, haloalkyl, alkoxy, alkoxycarbonyl, amino, alkylamino, haloalkoxy, alkylthio or aralkylthio), as the active principle and carrier.